If you think Disney World is just a theme park, you’re already starting off on the wrong foot. It’s not a park—it’s practically a city. Between figuring out transportation, park reservations, Lightning Lanes, dining, and resort logistics, it’s no wonder most first-timers feel overwhelmed.
But as someone who’s taken babies, toddlers, and big kids to Disney over a dozen times (and helped thousands of moms plan their trips inside my program Laid-back Magic®), I’ve noticed the same mistakes come up again and again.
Let’s break them down—and save you a whole lot of money, crankiness, and hangry toddler moments in the process.
It’s called Disney World for a reason. With 4 major parks, over 25 resorts, water parks, golf courses, two mini-cities (Disney Springs + BoardWalk), and a maze of buses, boats, monorails, and Skyliner gondolas… this isn’t your local Six Flags.
You’ll easily walk 7 to 10 miles a day, and it can take 40+ minutes to get from your resort room to the park entrance—especially if you’re relying on Disney buses with a double stroller.
If you treat Disney like a regular vacation, you’ll find yourself hot, frustrated, and hungry with no backup plan.
One of the most common Disney World planning mistakes: booking your park tickets and dining reservations before thinking through the order of your days.
Let’s say you book a dinner at Magic Kingdom, but you’re staying at a resort closest to EPCOT. Now your entire schedule—and transportation—is backwards. You’re forcing your family into a zig-zag itinerary that doesn’t make sense.
That’s why inside Laid-back Magic, I teach the “Sketch Method”: map out where you’ll be each day before touching reservations. Work backwards, not forwards.
Resort theming and waterslides are fun, but here’s the deal: the #1 factor that matters is location.
If your trip is focused on Magic Kingdom, it doesn’t make sense to stay at BoardWalk (even though I love it). Likewise, Caribbean Beach might have great Skyliner access, but if your days are heavy on Animal Kingdom or Disney Springs, you’ll spend half your trip on buses.
Instead, ask yourself:
Let’s paint a picture: you’re staying at Caribbean Beach and have breakfast at ‘Ohana in the Polynesian. What do you do?
You’ll need to know how to chain together a Skyliner + monorail combo and know which parts require collapsing your stroller. Most people only think about buses, but Disney has 4 different transportation systems—and they don’t all go everywhere.
Here’s a cheat sheet of what people get wrong:
If you learn just a little about transportation ahead of time, your whole day flows better.
Whether you’re planning sit-down character meals or just want quick lunch breaks, the food planning matters.
The My Disney Experience app’s mobile ordering system is great, but if you wait until everyone’s hungry, you’ll likely see 60–90 minute pickup windows. And nothing brings out the toddler meltdowns like hangry parents scrolling for snacks.
What to do instead:
You paid a lot for those tickets—so shouldn’t you stay open to close?
Not necessarily.
Burnout is real, especially with young kids. Trying to power through a 14-hour park day is a recipe for tears (theirs and yours). A midday break at the pool or a nap at the resort could actually extend your trip stamina by days.
Getting your “money’s worth” might mean taking a break, not pushing through.
I’ve taken kids to Disney at 6 weeks, 6 months, 2 years, 5 years, 9 years… and here’s what I’ve learned: there is no perfect age.
There are easier ages, sure. My toddler still naps in a stroller (a win), but isn’t potty trained (a tradeoff). My older daughter doesn’t nap—but she now has opinions about rides and restaurants and souvenirs (also a tradeoff).
No matter the age, there’s something magical that clicks. Sometimes it’s a ride. Sometimes it’s a show. Sometimes it’s simply a moment where you see the sparkle in their eyes. Don’t wait for perfect.
Travel agents are incredible, and many of them are friends of mine.
But Disney World isn’t a “book it and show up” vacation. Even with a travel agent or guide, you still need to know your own priorities. You still need to understand what park you’re going to first, how transportation works, how to use Lightning Lanes, and what time of day you want to eat.
This is why Laid-back Magic isn’t a concierge—it’s a toolkit to help you learn how to think through your Disney trip.
That’s exactly why I created Laid-back Magic®, the no-fluff planning guide + private community for moms who want a smoother Disney trip without spending 90 hours on YouTube.
Inside, you’ll get:
Join the Laid-Back Magic® community – use the word PODCAST for a discount!
Join the Laid-Back Magic® community
Podcast music by Podington Bear, track: ‘Filaments’, licensed under CC BY-NC, courtesy of Free Music Archive.
[00:00:00] Dana Stanley: If you’ve ever thought, uh, it just seems like a lot when talking about planning a Disney World trip. This episode is for you because I’ve found that Disney does take effort, but what most people get wrong is where to put that effort. And just like the people, and just like the people we met on a plane to Eleuthra who didn’t know which island they were actually staying on, which I’m gonna tell you that story in a bit.
[00:00:27] Dana Stanley: You don’t wanna land in Orlando without a clue of what’s going on. So in this episode, I’m walking you through the things I see families get wrong over and over again about Disney World and how to make better, smarter, and also more laid back decisions instead. Let’s get into it
[00:00:43] Dana Stanley: if we haven’t already met. Hello, I’m Dana. I’m a mom of three who has seen dozens and dozens of trips for obviously my own family, but hundreds more through my planning community. And one thing I’ve noticed is that there’re just like certain things over and over again that people just get wrong about Disney World.
[00:01:03] Dana Stanley: Whether it be straight up misconceptions or maybe just focusing on the wrong thing, the first thing I see most people get wrong when it comes to Disney World. Is thinking that it requires too much planning, so it’s just not worth it. I recently got a comment on a reel last week where someone actually used the word scared when describing what they thought about going back to Disney World after 10 plus years of not visiting the parks.
[00:01:35] Dana Stanley: And what can happen is one of two things. First, they either do not go to Disney World. They choose to just avoid it, which fine, like that’s definitely a decision or two, they still wanna go to Disney World, but they’re just not convinced that it requires that much work. Like they think, well, I didn’t do it 10 years ago.
[00:01:57] Dana Stanley: People are just overboard nowadays. Like when I did this back in X, Y, Z year, we had a great time and we didn’t have to do all this. Electronic stuff and all the planning and all the things, we’re gonna just go with the flow.
[00:02:10] Dana Stanley: As soon as I was writing out the notes for this episode, it brought up a memory about a trip when we were going to The Bahamas and we were staying on an island called Eleuthera. So a little backstory is that there is an island called Harbor Island down in The Bahamas that’s really small and magical.
[00:02:29] Dana Stanley: By the way, you should definitely go, but there’s no airport. It’s just too small to have a landing strip. So to get there, you have to fly to a Lutheran, which is right next door, and then you can take a little boat over to Harbor Island.
[00:02:43] Dana Stanley: And we had a layover on this trip, and during the layover, my daughter made friends with someone else that was also flying to Eleuthera. They were like the same age. We were essentially getting on the next plane together and on the second leg we were on a smaller plane and ended up being right next to this family.
[00:03:01] Dana Stanley: So we’re chatting about the girls and where we’re staying, where they’re staying, and when I asked them where they were staying. They kind of said it with like a question mark. They were like Harbor Island. And so obviously that made me a little bit nervous. So when I asked the name of the hotel that they were staying at, we knew that that hotel was not on Harbor Island, it was on a Lutheran.
[00:03:26] Dana Stanley: They just didn’t realize that they were two completely separate islands. They were kind of combining in their minds, a Lutheran and Harbor Island and thinking it was all the same place when there’s like water between them.
[00:03:38] Dana Stanley: All this to say, were they fine? Sure. Did they have a great time? I’m sure. Did it technically matter that they stayed on one island and not the other? Probably not. But then the more realistic things is if they had done any research, which it didn’t seem like they did, honestly. But all like the restaurants you would see and like cool things on Harbor Island.
[00:04:04] Dana Stanley: Maybe you really wanted to go to X, Y, Z, but now you know that there’s like a boat ride between those things. Or maybe they rented a golf cart on Harbor Island thinking that they could just use that to get around. Didn’t need a car. But now they’re not on that island. They’re on this huge island and can’t easily get around because they don’t have a car.
[00:04:24] Dana Stanley: Now if you’re listening to this, I doubt you’re one of those people that would like get on a plane not really knowing exactly where they were landing. You probably appreciate and understand that a little bit of knowledge ahead of time opens up like a whole world of your vacation. Just knowing certain things ahead of time, and I’m certainly not saying that everything can be a hundred percent predicted.
[00:04:51] Dana Stanley: But that’s the mistake I see people make is like figuratively speaking hobbing on a plane because they just don’t want to deal with the planning of it and they still wanna go anyway. And I do think for certain situations within Disney World that you can, like, you can be a little spontaneous, but you don’t wanna leave certain things to chance when it comes to.
[00:05:16] Dana Stanley: Getting somewhere in Disney World maybe promises you make to your kids that you can’t keep, that you realize later your expectations, making sure you booked the correct room or room type.
[00:05:29] Dana Stanley: For example, I chat with a lot of people that stay at the Swan Dolphin or Swan Reserve in Disney World, and it’s very close to my favorite resort, the Boardwalk. I really love that whole area called Crescent Lake and the Swan and Dolphin. There’s a lot of great things about these spots. It’s very affordable.
[00:05:48] Dana Stanley: It’s owned by Marriott. A lot of people use points. The restaurants are pretty good and. Like I said, it’s just in a great spot. I think the best spot to stay on Disney property in that vicinity. That being said, some people will stay there. They sometimes, not always, but they won’t have a grasp on like the logistics of the resort.
[00:06:13] Dana Stanley: Like for instance, you can’t use your magic band once you’re in the hotel because technically it’s not owned and operated by Disney. So you can’t use it as your room key. You can’t charge things to the room. And I’ve heard of people you know, investing in magic bands, and then they’re annoyed that they can’t use them at the hotel.
[00:06:34] Dana Stanley: Another downside is that the bus won’t take you directly to Magic Kingdom. It’s actually going to drop you off. At the Ticket and Transportation Center first, and then you have to get from there to the Magic Kingdom Gates. And I would say 99% of things that you hear people complain about in Disney World is just like those people on the plane.
[00:06:56] Dana Stanley: They just didn’t know. They didn’t realize it. If they had known that about the bus, they would’ve known that if they just walked next door to Beach Club or even Boardwalks bus stop, they could go straight to Magic Kingdom and it would’ve been a lot faster.
[00:07:09] Dana Stanley: I didn’t realize how important this next thinking was until I didn’t realize how important this one was until I became a mom, honestly, and had to start thinking about. More of the logistics with kids and just getting around from point A to point B from, you know, our stroller, a single stroller, a double stroller to car seats.
[00:07:34] Dana Stanley: So if you wanna, imagine you are in Disney World and you’re staying at Caribbean Beach Resort and you have a breakfast reservation at Ohana, what do you do? Some people think, oh, like we’re just gonna take all of the buses when we get to Disney. I’ve heard that you can’t. I’ve heard that you don’t need car seats on buses and they’re free, but they don’t realize that some situations there isn’t a bus option, like getting from resort to resort a bus might be one leg of getting from point A to point B, but then you end up kind of going all over creation and you end up being late and now you’re sweaty and rushing when you get there and it’s just like not a good feeling if you’re going to Disney World for the first time or the first time with kids.
[00:08:19] Dana Stanley: You’ll need to have just a basic understanding of the buses, monorail boats, and the skyliner, and just know which ones you need to collapse your stroller for and which ones you can walk on.
[00:08:32] Dana Stanley: People get it wrong thinking that like it’s just a theme park and it’ll be easy to get around, but it’s big, like it’s really a whole Disney world. This was one of the first like playful arguments my husband and I had when we first started dating because I grew up going to Disneyland and I kind of was messing with him that it was better because it was the original.
[00:08:56] Dana Stanley: But he grew up going to Disney World and his take was, yeah, Walt made Disneyland and it was like, fine. And then he was like, how can I make it better? And he made Disney World. And while that’s a conversation for another day. It is true that when it comes to Disney World, W-O-R-L-D, it’s not this little theme park like it’s a small city.
[00:09:19] Dana Stanley: You’re gonna walk seven, maybe 10 miles a day, depending on the park, and then it can take 40 plus minutes to get from your hotel to the park entrance, depending on where you’re staying.
[00:09:32] Dana Stanley: And that adds up quickly when you’re hauling kids and a stroller and managing everything else.
[00:09:38] Dana Stanley: And that catches up to people quickly when they don’t realize like how big the property actually is. And they waited until the last minute to figure out how to get somewhere. And it’s just like. It’s not fun. It’s not a fun feeling, and I see it all the time and it makes me sad because if you just take like five minutes literally on the plane down if you wanted to, and just click around Google Maps, you can get a bearing as to how to get, you can have a bearing of how to get around now.
[00:10:09] Dana Stanley: Now, this next one feels small, but it actually changes everything once you’re in the thick of the trip, like once you’re. Like boots on the ground doing the thing. And I don’t think it gets talked about enough. And that’s that most people will choose the resort over almost everything. But the location itself, and I mean, what I mean is they’re looking at the price the pool, the theming.
[00:10:38] Dana Stanley: I get a lot of questions, for example, like which pool is best for toddlers, et cetera. And I think the question is. Where is the resort physically located, and then what is the best for toddlers in that sense? Because it’s going to be what you’ll end up caring about the most. Now, if there are two resorts that are, let’s say in the same vicinity like Porter versus French Quarter, or Boardwalk versus Beach Club, or Kani Village versus Jambo House, then totally let’s get into the minutiae of the lobby or the pool, or you know, the restaurants.
[00:11:17] Dana Stanley: A hundred percent, yes. But the first thing I think you should think about. When you’re deciding a resort is where will you be spending the most time?
[00:11:26] Dana Stanley: For example, boardwalk is hands down my favorite resort, but if you posted in my forum, Hey Dana, we have a short weekend trip because my husband has a conference in Orlando and we decided we’re only visiting Magic Kingdom and we have Christmas party tickets. I wouldn’t necessarily be gung-ho for you to stay at Boardwalk.
[00:11:49] Dana Stanley: It wouldn’t really make sense to stay in the boardwalk area where you can walk or take a boat to Epcot and Hollywood Studios when you’re not even visiting those parks.
[00:11:58] Dana Stanley: After you know where you’ll be going the most, then you can work backwards from there and see which resorts are closest to that park, and then get into the nitty gritty of what you think is best for your family and your budget.
[00:12:09] Dana Stanley: And that brings me to something else people don’t always consider until they’re already, again in the thick of it, they’re already there. And that’s thinking that they’re just going to quote, grab something to eat. I don’t care if you are bringing a sack lunch to the parks or doing sit down dining for breakfast, lunch and dinner, please.
[00:12:31] Dana Stanley: I just want everyone to know where they’re going to eat. I can’t even tell you how many times I just want a snack, like, oh, I’m not that hungry. We’re just gonna grab a snack. And we will be in a vicinity where there are truly no snacks. And when you have three kids, it’s a bigger deal to schlep like halfway across the park for something that’s just supposed to be easy.
[00:12:55] Dana Stanley: It ends up being like the opposite of easy. I found. The more I think that I’m gonna do something, chill and I always regret it.
[00:13:02] Dana Stanley: So now I just know what food spots we’re going to be around. Breakfast, lunch, and dinner, just the vicinity, which ones I have dining reservations for, and if we are gonna do quick service, which ones have mobile Order ahead so that my kids don’t get cranky because mobile ordering is amazing. When you plan ahead a little bit, if you wait until you’re hungry, sometimes the spot’s already filled up.
[00:13:27] Dana Stanley: Maybe you hit the button and you realize your food’s not gonna be ready for 45 minutes.
[00:13:32] Dana Stanley: Or if you’re mobile ordering, I mean, it takes a little bit of time. Like I have to sit down. We have five people. I have to sit down and tell Colton like, all right, like, roll up my sleeves. I’m about to mobile order. I feel like this gets overlooked. A lot of just the brain power that goes into a lot of these things.
[00:13:50] Dana Stanley: And it’s not, and it is infinitely easier when you’ve thought about it ahead of time instead of like being caught off guard. And just a little tip, since you’ll be hitting the I Am Here button, when you arrive at the Quick Service location to let them know that you’re there to put out your food, you can hit that button a little early.
[00:14:13] Dana Stanley: So I’ve waited anywhere from like five to 20 minutes at these mobile order spots after I hit the button. So now I just kind of hit it when I’m like headed there, like, okay, we’re walking to said location and it usually ends up being perfect. Like I’m kind of waltzing up when I get the alert that my food is ready magical.
[00:14:34] Dana Stanley: Another thing I see a lot is that you can and or should stay in the park all day long. I know I’ve talked about this on the podcast before about how one of the most difficult things about enjoying a Disney trip and setting expectations is that it’s so expensive and it is a lot of work. And because of that, some people feel like they need to like get their money’s worth.
[00:15:02] Dana Stanley: And I totally, I mean, listen, I totally get that. But when you think about what is going on to make things enjoyable. It may not be getting there the minute it opens and staying till after it closed, like that might not actually be enjoyable, and then you’re doing the opposite of what you’re trying to do.
[00:15:24] Dana Stanley: It may be that getting your quote money’s worth is actually taking a break or going to the pool or being there less time.
[00:15:32] Dana Stanley: It’s funny because this next one feels obvious, I think, for people that have gone to Disney World. Over the years, or maybe like yearly vacations, but if you’re new to Disney or you haven’t taken the kids yet, you’d probably never guess that there really isn’t a perfect age for Disney. So a lot of people get it wrong that they’re waiting for this elusive perfect age
[00:15:58] Dana Stanley: now that I’ve taken truly. Like truly every age to Disney World from six weeks to nine years old. Between, you know, like staggering the three kids as they’ve grown up and they, and none of them were born around the same time of year. So really just every age between those are some ages easier in terms of logistics.
[00:16:22] Dana Stanley: Absolutely. For example, sailor or Middle, she just reached the height limit where a lot of rides open up, I think she can only not ride two things. So it’s nice. Like we don’t necessarily have, like, it’s nice that we’re able to like bring her with story now and we can like all ride together on these bigger rides.
[00:16:45] Dana Stanley: But now that she’s older, she also has more opinions and she wants more souvenirs. She is at that age where she’s too old to nap. But she like kind of could use a nap. So she gets very, so she gets very cranky at the end of the day. In some ways, a little bit, in some ways needs an earlier bedtime than my toddler who does nap because she’s toast, like she’s exhausted.
[00:17:17] Dana Stanley: And then crew is almost two years old and he’s very, very difficult in some ways. He doesn’t wanna sit down, he. For sure, like, I mean, you know, if you’re a parent, like two years old is very hard, but he’s not potty trained yet, so we’re not taking potty breaks with him. And then he also takes a nap and in the middle of the day, so we get that little reset, he gets a reset and he’s free since he’s under three and he’s not even quite two yet.
[00:17:45] Dana Stanley: So even under two, like the flight down, we can have him as a lap infant, also free on the flight. So he’s harder. In some ways, but it’s kind of nice that we don’t have to pay for him.
[00:17:58] Dana Stanley: All that being said, and I know that Disney people understand this, that there is pros and cons, if you wanna call it magic at every age. There have been trips where maybe my one 4-year-old, it was like a magical, easy trip, but then my other. But then their sibling, when they were four was really hard. You just don’t know.
[00:18:19] Dana Stanley: Everyone has different personalities. Every kid is struggling with different development things at different ages. So when you’re waiting for this perfect thing, or you think they’re gonna remember things, there’s always, for every plus, just know that there’s gonna be a minus. I guarantee that there’s going to be something on the trip that they lock onto and like that’s their version of magic.
[00:18:44] Dana Stanley: And it doesn’t matter if they’re like six weeks. Okay? Six weeks is pretty young. I don’t know if they’re seeing magic, but from little to nine years old, whether it be a character or seeing a train or seeing fireworks for the first time, like you can see it when it clicks for them.
[00:19:01] Dana Stanley: Like you can see it when it clicks for them. And even more than that, I think a lot of people just don’t know what they don’t know. And this next one is a perfect example.
[00:19:12] Dana Stanley: One of the biggest ones for me is booking your tickets and dining reservations First. What can happen when you skip what I call a sketch? Is now you’re kind of stuck with these concrete things like we’re visiting the parks from this date to this date and you get tickets for those days, which could be more or less than what you need.
[00:19:35] Dana Stanley: Then you have like set dining reservations that you don’t wanna cancel ’cause they were hard to get. What ends up happening is you’re like pigeonholing yourself and your plans to now fit around these things, but it should be the other way around. Most people think Disney planning is like. Any other trip, like you grab a hotel, you grab some tickets and you show up.
[00:19:56] Dana Stanley: But really without at least a loose sketch, you will, you could end up wasting a ton of time in lines missing, like big experiences that you’re hoping you could have and then spend more money fixing like last minute problems. I’ve seen this many, many times. There is one word that has changed the way I market my business completely over the years, and that word is stress free.
[00:20:25] Dana Stanley: Stress free used to be in my copy and all over my website, all over my Instagram in the beginning, and I found just as my business grew, the more I was online, the more I started talking with people and learning even more about Disney planning. And going to Disney World more,
[00:20:43] Dana Stanley: you know, it was like a disservice to say, you know, join laid back magic for a stress-free Disney trip. Or I’ve seen a rent this stroller for a stress-free trip. Or hire this travel agent for a stress-free vacation.
[00:21:00] Dana Stanley: And that’s the mistake of thinking. If I just do this one thing, if I just kind of hand this off, that your vacation itself will be free of stress.
[00:21:11] Dana Stanley: Can it lessen the stress? For sure. Can it make the planning itself less stressful? A hundred percent. But the vacation itself, especially with kids traveling in general is going to be a lot on your stress levels. It just is. It’s a lot to think about at once. There’s a lot going on all at once. It’s a long day.
[00:21:39] Dana Stanley: Even if you’re taking breaks, it’s just an unusual day that you aren’t used to, that your kids aren’t used to.
[00:21:45] Dana Stanley: You’re gonna have your kids and family. Maybe you’re in like a little studio together 24 7, which honestly is like pretty close to my normal, but I know it’s not for everyone. And that can be like a pretty stressful experience if you’re not used to it.
[00:21:59] Dana Stanley: And if you’re anything like me of just like being in a woman’s body when she had a kid.
[00:22:05] Dana Stanley: Two, three, even four years ago. Like there are chemicals and hormones that, like there are chemicals and hormones that you, and I don’t even understand what is going on, like the turmoil inside of us. And I’m pretty sure no service in the world can take that away.
[00:22:25] Dana Stanley: So can these things lessen the stress, especially like all compounded together? Yes. But don’t set the expectation that the trip is going to be stress free. That’s just a crazy thing for anyone to try and promise or g.
[00:22:42] Dana Stanley: But don’t set yourself up with the expectation that because I did X, Y, Z or used X, Y, Z, this trip is going to be stress free. I feel like that’s just a crazy thing for anyone to try and guarantee
[00:22:57] Dana Stanley: if any of these things. Made your stomach twist a little. That is not a sign that you think or you’re doing anything wrong. It just means that you care about your trip, which is great. I’ve made some of these mistakes too, and that’s exactly why I created Laid Back Magic in the first place, so that there was like, so that I could have a clear roadmap that I could repeat for every single trip with the actual steps to take, so I knew what to focus on and when all in one place.
[00:23:29] Dana Stanley: I’ll link it for you below, or just head to laidbackmagic.com and use the word podcast to get a special price as a thank you for listening to the show.
My life doesn't revolve around Disney like you may think. I live for my family: my husband and our three kids. In my spare time I like to make my home the best it can be, read on our porch and watch (you guessed it) Disney+.
If you think Disney World is just a theme park, you’re already starting off on the wrong foot. It’s not a park—it’s practically a city. Between figuring out transportation, park reservations, Lightning Lanes, dining, and resort logistics, it’s no wonder most first-timers feel overwhelmed.
But as someone who’s taken babies, toddlers, and big kids to Disney over a dozen times (and helped thousands of moms plan their trips inside my program Laid-back Magic®), I’ve noticed the same mistakes come up again and again.
Let’s break them down—and save you a whole lot of money, crankiness, and hangry toddler moments in the process.
It’s called Disney World for a reason. With 4 major parks, over 25 resorts, water parks, golf courses, two mini-cities (Disney Springs + BoardWalk), and a maze of buses, boats, monorails, and Skyliner gondolas… this isn’t your local Six Flags.
You’ll easily walk 7 to 10 miles a day, and it can take 40+ minutes to get from your resort room to the park entrance—especially if you’re relying on Disney buses with a double stroller.
If you treat Disney like a regular vacation, you’ll find yourself hot, frustrated, and hungry with no backup plan.
One of the most common Disney World planning mistakes: booking your park tickets and dining reservations before thinking through the order of your days.
Let’s say you book a dinner at Magic Kingdom, but you’re staying at a resort closest to EPCOT. Now your entire schedule—and transportation—is backwards. You’re forcing your family into a zig-zag itinerary that doesn’t make sense.
That’s why inside Laid-back Magic, I teach the “Sketch Method”: map out where you’ll be each day before touching reservations. Work backwards, not forwards.
Resort theming and waterslides are fun, but here’s the deal: the #1 factor that matters is location.
If your trip is focused on Magic Kingdom, it doesn’t make sense to stay at BoardWalk (even though I love it). Likewise, Caribbean Beach might have great Skyliner access, but if your days are heavy on Animal Kingdom or Disney Springs, you’ll spend half your trip on buses.
Instead, ask yourself:
Let’s paint a picture: you’re staying at Caribbean Beach and have breakfast at ‘Ohana in the Polynesian. What do you do?
You’ll need to know how to chain together a Skyliner + monorail combo and know which parts require collapsing your stroller. Most people only think about buses, but Disney has 4 different transportation systems—and they don’t all go everywhere.
Here’s a cheat sheet of what people get wrong:
If you learn just a little about transportation ahead of time, your whole day flows better.
Whether you’re planning sit-down character meals or just want quick lunch breaks, the food planning matters.
The My Disney Experience app’s mobile ordering system is great, but if you wait until everyone’s hungry, you’ll likely see 60–90 minute pickup windows. And nothing brings out the toddler meltdowns like hangry parents scrolling for snacks.
What to do instead:
You paid a lot for those tickets—so shouldn’t you stay open to close?
Not necessarily.
Burnout is real, especially with young kids. Trying to power through a 14-hour park day is a recipe for tears (theirs and yours). A midday break at the pool or a nap at the resort could actually extend your trip stamina by days.
Getting your “money’s worth” might mean taking a break, not pushing through.
I’ve taken kids to Disney at 6 weeks, 6 months, 2 years, 5 years, 9 years… and here’s what I’ve learned: there is no perfect age.
There are easier ages, sure. My toddler still naps in a stroller (a win), but isn’t potty trained (a tradeoff). My older daughter doesn’t nap—but she now has opinions about rides and restaurants and souvenirs (also a tradeoff).
No matter the age, there’s something magical that clicks. Sometimes it’s a ride. Sometimes it’s a show. Sometimes it’s simply a moment where you see the sparkle in their eyes. Don’t wait for perfect.
Travel agents are incredible, and many of them are friends of mine.
But Disney World isn’t a “book it and show up” vacation. Even with a travel agent or guide, you still need to know your own priorities. You still need to understand what park you’re going to first, how transportation works, how to use Lightning Lanes, and what time of day you want to eat.
This is why Laid-back Magic isn’t a concierge—it’s a toolkit to help you learn how to think through your Disney trip.
That’s exactly why I created Laid-back Magic®, the no-fluff planning guide + private community for moms who want a smoother Disney trip without spending 90 hours on YouTube.
Inside, you’ll get:
Join the Laid-Back Magic® community – use the word PODCAST for a discount!
Join the Laid-Back Magic® community
Podcast music by Podington Bear, track: ‘Filaments’, licensed under CC BY-NC, courtesy of Free Music Archive.
[00:00:00] Dana Stanley: If you’ve ever thought, uh, it just seems like a lot when talking about planning a Disney World trip. This episode is for you because I’ve found that Disney does take effort, but what most people get wrong is where to put that effort. And just like the people, and just like the people we met on a plane to Eleuthra who didn’t know which island they were actually staying on, which I’m gonna tell you that story in a bit.
[00:00:27] Dana Stanley: You don’t wanna land in Orlando without a clue of what’s going on. So in this episode, I’m walking you through the things I see families get wrong over and over again about Disney World and how to make better, smarter, and also more laid back decisions instead. Let’s get into it
[00:00:43] Dana Stanley: if we haven’t already met. Hello, I’m Dana. I’m a mom of three who has seen dozens and dozens of trips for obviously my own family, but hundreds more through my planning community. And one thing I’ve noticed is that there’re just like certain things over and over again that people just get wrong about Disney World.
[00:01:03] Dana Stanley: Whether it be straight up misconceptions or maybe just focusing on the wrong thing, the first thing I see most people get wrong when it comes to Disney World. Is thinking that it requires too much planning, so it’s just not worth it. I recently got a comment on a reel last week where someone actually used the word scared when describing what they thought about going back to Disney World after 10 plus years of not visiting the parks.
[00:01:35] Dana Stanley: And what can happen is one of two things. First, they either do not go to Disney World. They choose to just avoid it, which fine, like that’s definitely a decision or two, they still wanna go to Disney World, but they’re just not convinced that it requires that much work. Like they think, well, I didn’t do it 10 years ago.
[00:01:57] Dana Stanley: People are just overboard nowadays. Like when I did this back in X, Y, Z year, we had a great time and we didn’t have to do all this. Electronic stuff and all the planning and all the things, we’re gonna just go with the flow.
[00:02:10] Dana Stanley: As soon as I was writing out the notes for this episode, it brought up a memory about a trip when we were going to The Bahamas and we were staying on an island called Eleuthera. So a little backstory is that there is an island called Harbor Island down in The Bahamas that’s really small and magical.
[00:02:29] Dana Stanley: By the way, you should definitely go, but there’s no airport. It’s just too small to have a landing strip. So to get there, you have to fly to a Lutheran, which is right next door, and then you can take a little boat over to Harbor Island.
[00:02:43] Dana Stanley: And we had a layover on this trip, and during the layover, my daughter made friends with someone else that was also flying to Eleuthera. They were like the same age. We were essentially getting on the next plane together and on the second leg we were on a smaller plane and ended up being right next to this family.
[00:03:01] Dana Stanley: So we’re chatting about the girls and where we’re staying, where they’re staying, and when I asked them where they were staying. They kind of said it with like a question mark. They were like Harbor Island. And so obviously that made me a little bit nervous. So when I asked the name of the hotel that they were staying at, we knew that that hotel was not on Harbor Island, it was on a Lutheran.
[00:03:26] Dana Stanley: They just didn’t realize that they were two completely separate islands. They were kind of combining in their minds, a Lutheran and Harbor Island and thinking it was all the same place when there’s like water between them.
[00:03:38] Dana Stanley: All this to say, were they fine? Sure. Did they have a great time? I’m sure. Did it technically matter that they stayed on one island and not the other? Probably not. But then the more realistic things is if they had done any research, which it didn’t seem like they did, honestly. But all like the restaurants you would see and like cool things on Harbor Island.
[00:04:04] Dana Stanley: Maybe you really wanted to go to X, Y, Z, but now you know that there’s like a boat ride between those things. Or maybe they rented a golf cart on Harbor Island thinking that they could just use that to get around. Didn’t need a car. But now they’re not on that island. They’re on this huge island and can’t easily get around because they don’t have a car.
[00:04:24] Dana Stanley: Now if you’re listening to this, I doubt you’re one of those people that would like get on a plane not really knowing exactly where they were landing. You probably appreciate and understand that a little bit of knowledge ahead of time opens up like a whole world of your vacation. Just knowing certain things ahead of time, and I’m certainly not saying that everything can be a hundred percent predicted.
[00:04:51] Dana Stanley: But that’s the mistake I see people make is like figuratively speaking hobbing on a plane because they just don’t want to deal with the planning of it and they still wanna go anyway. And I do think for certain situations within Disney World that you can, like, you can be a little spontaneous, but you don’t wanna leave certain things to chance when it comes to.
[00:05:16] Dana Stanley: Getting somewhere in Disney World maybe promises you make to your kids that you can’t keep, that you realize later your expectations, making sure you booked the correct room or room type.
[00:05:29] Dana Stanley: For example, I chat with a lot of people that stay at the Swan Dolphin or Swan Reserve in Disney World, and it’s very close to my favorite resort, the Boardwalk. I really love that whole area called Crescent Lake and the Swan and Dolphin. There’s a lot of great things about these spots. It’s very affordable.
[00:05:48] Dana Stanley: It’s owned by Marriott. A lot of people use points. The restaurants are pretty good and. Like I said, it’s just in a great spot. I think the best spot to stay on Disney property in that vicinity. That being said, some people will stay there. They sometimes, not always, but they won’t have a grasp on like the logistics of the resort.
[00:06:13] Dana Stanley: Like for instance, you can’t use your magic band once you’re in the hotel because technically it’s not owned and operated by Disney. So you can’t use it as your room key. You can’t charge things to the room. And I’ve heard of people you know, investing in magic bands, and then they’re annoyed that they can’t use them at the hotel.
[00:06:34] Dana Stanley: Another downside is that the bus won’t take you directly to Magic Kingdom. It’s actually going to drop you off. At the Ticket and Transportation Center first, and then you have to get from there to the Magic Kingdom Gates. And I would say 99% of things that you hear people complain about in Disney World is just like those people on the plane.
[00:06:56] Dana Stanley: They just didn’t know. They didn’t realize it. If they had known that about the bus, they would’ve known that if they just walked next door to Beach Club or even Boardwalks bus stop, they could go straight to Magic Kingdom and it would’ve been a lot faster.
[00:07:09] Dana Stanley: I didn’t realize how important this next thinking was until I didn’t realize how important this one was until I became a mom, honestly, and had to start thinking about. More of the logistics with kids and just getting around from point A to point B from, you know, our stroller, a single stroller, a double stroller to car seats.
[00:07:34] Dana Stanley: So if you wanna, imagine you are in Disney World and you’re staying at Caribbean Beach Resort and you have a breakfast reservation at Ohana, what do you do? Some people think, oh, like we’re just gonna take all of the buses when we get to Disney. I’ve heard that you can’t. I’ve heard that you don’t need car seats on buses and they’re free, but they don’t realize that some situations there isn’t a bus option, like getting from resort to resort a bus might be one leg of getting from point A to point B, but then you end up kind of going all over creation and you end up being late and now you’re sweaty and rushing when you get there and it’s just like not a good feeling if you’re going to Disney World for the first time or the first time with kids.
[00:08:19] Dana Stanley: You’ll need to have just a basic understanding of the buses, monorail boats, and the skyliner, and just know which ones you need to collapse your stroller for and which ones you can walk on.
[00:08:32] Dana Stanley: People get it wrong thinking that like it’s just a theme park and it’ll be easy to get around, but it’s big, like it’s really a whole Disney world. This was one of the first like playful arguments my husband and I had when we first started dating because I grew up going to Disneyland and I kind of was messing with him that it was better because it was the original.
[00:08:56] Dana Stanley: But he grew up going to Disney World and his take was, yeah, Walt made Disneyland and it was like, fine. And then he was like, how can I make it better? And he made Disney World. And while that’s a conversation for another day. It is true that when it comes to Disney World, W-O-R-L-D, it’s not this little theme park like it’s a small city.
[00:09:19] Dana Stanley: You’re gonna walk seven, maybe 10 miles a day, depending on the park, and then it can take 40 plus minutes to get from your hotel to the park entrance, depending on where you’re staying.
[00:09:32] Dana Stanley: And that adds up quickly when you’re hauling kids and a stroller and managing everything else.
[00:09:38] Dana Stanley: And that catches up to people quickly when they don’t realize like how big the property actually is. And they waited until the last minute to figure out how to get somewhere. And it’s just like. It’s not fun. It’s not a fun feeling, and I see it all the time and it makes me sad because if you just take like five minutes literally on the plane down if you wanted to, and just click around Google Maps, you can get a bearing as to how to get, you can have a bearing of how to get around now.
[00:10:09] Dana Stanley: Now, this next one feels small, but it actually changes everything once you’re in the thick of the trip, like once you’re. Like boots on the ground doing the thing. And I don’t think it gets talked about enough. And that’s that most people will choose the resort over almost everything. But the location itself, and I mean, what I mean is they’re looking at the price the pool, the theming.
[00:10:38] Dana Stanley: I get a lot of questions, for example, like which pool is best for toddlers, et cetera. And I think the question is. Where is the resort physically located, and then what is the best for toddlers in that sense? Because it’s going to be what you’ll end up caring about the most. Now, if there are two resorts that are, let’s say in the same vicinity like Porter versus French Quarter, or Boardwalk versus Beach Club, or Kani Village versus Jambo House, then totally let’s get into the minutiae of the lobby or the pool, or you know, the restaurants.
[00:11:17] Dana Stanley: A hundred percent, yes. But the first thing I think you should think about. When you’re deciding a resort is where will you be spending the most time?
[00:11:26] Dana Stanley: For example, boardwalk is hands down my favorite resort, but if you posted in my forum, Hey Dana, we have a short weekend trip because my husband has a conference in Orlando and we decided we’re only visiting Magic Kingdom and we have Christmas party tickets. I wouldn’t necessarily be gung-ho for you to stay at Boardwalk.
[00:11:49] Dana Stanley: It wouldn’t really make sense to stay in the boardwalk area where you can walk or take a boat to Epcot and Hollywood Studios when you’re not even visiting those parks.
[00:11:58] Dana Stanley: After you know where you’ll be going the most, then you can work backwards from there and see which resorts are closest to that park, and then get into the nitty gritty of what you think is best for your family and your budget.
[00:12:09] Dana Stanley: And that brings me to something else people don’t always consider until they’re already, again in the thick of it, they’re already there. And that’s thinking that they’re just going to quote, grab something to eat. I don’t care if you are bringing a sack lunch to the parks or doing sit down dining for breakfast, lunch and dinner, please.
[00:12:31] Dana Stanley: I just want everyone to know where they’re going to eat. I can’t even tell you how many times I just want a snack, like, oh, I’m not that hungry. We’re just gonna grab a snack. And we will be in a vicinity where there are truly no snacks. And when you have three kids, it’s a bigger deal to schlep like halfway across the park for something that’s just supposed to be easy.
[00:12:55] Dana Stanley: It ends up being like the opposite of easy. I found. The more I think that I’m gonna do something, chill and I always regret it.
[00:13:02] Dana Stanley: So now I just know what food spots we’re going to be around. Breakfast, lunch, and dinner, just the vicinity, which ones I have dining reservations for, and if we are gonna do quick service, which ones have mobile Order ahead so that my kids don’t get cranky because mobile ordering is amazing. When you plan ahead a little bit, if you wait until you’re hungry, sometimes the spot’s already filled up.
[00:13:27] Dana Stanley: Maybe you hit the button and you realize your food’s not gonna be ready for 45 minutes.
[00:13:32] Dana Stanley: Or if you’re mobile ordering, I mean, it takes a little bit of time. Like I have to sit down. We have five people. I have to sit down and tell Colton like, all right, like, roll up my sleeves. I’m about to mobile order. I feel like this gets overlooked. A lot of just the brain power that goes into a lot of these things.
[00:13:50] Dana Stanley: And it’s not, and it is infinitely easier when you’ve thought about it ahead of time instead of like being caught off guard. And just a little tip, since you’ll be hitting the I Am Here button, when you arrive at the Quick Service location to let them know that you’re there to put out your food, you can hit that button a little early.
[00:14:13] Dana Stanley: So I’ve waited anywhere from like five to 20 minutes at these mobile order spots after I hit the button. So now I just kind of hit it when I’m like headed there, like, okay, we’re walking to said location and it usually ends up being perfect. Like I’m kind of waltzing up when I get the alert that my food is ready magical.
[00:14:34] Dana Stanley: Another thing I see a lot is that you can and or should stay in the park all day long. I know I’ve talked about this on the podcast before about how one of the most difficult things about enjoying a Disney trip and setting expectations is that it’s so expensive and it is a lot of work. And because of that, some people feel like they need to like get their money’s worth.
[00:15:02] Dana Stanley: And I totally, I mean, listen, I totally get that. But when you think about what is going on to make things enjoyable. It may not be getting there the minute it opens and staying till after it closed, like that might not actually be enjoyable, and then you’re doing the opposite of what you’re trying to do.
[00:15:24] Dana Stanley: It may be that getting your quote money’s worth is actually taking a break or going to the pool or being there less time.
[00:15:32] Dana Stanley: It’s funny because this next one feels obvious, I think, for people that have gone to Disney World. Over the years, or maybe like yearly vacations, but if you’re new to Disney or you haven’t taken the kids yet, you’d probably never guess that there really isn’t a perfect age for Disney. So a lot of people get it wrong that they’re waiting for this elusive perfect age
[00:15:58] Dana Stanley: now that I’ve taken truly. Like truly every age to Disney World from six weeks to nine years old. Between, you know, like staggering the three kids as they’ve grown up and they, and none of them were born around the same time of year. So really just every age between those are some ages easier in terms of logistics.
[00:16:22] Dana Stanley: Absolutely. For example, sailor or Middle, she just reached the height limit where a lot of rides open up, I think she can only not ride two things. So it’s nice. Like we don’t necessarily have, like, it’s nice that we’re able to like bring her with story now and we can like all ride together on these bigger rides.
[00:16:45] Dana Stanley: But now that she’s older, she also has more opinions and she wants more souvenirs. She is at that age where she’s too old to nap. But she like kind of could use a nap. So she gets very, so she gets very cranky at the end of the day. In some ways, a little bit, in some ways needs an earlier bedtime than my toddler who does nap because she’s toast, like she’s exhausted.
[00:17:17] Dana Stanley: And then crew is almost two years old and he’s very, very difficult in some ways. He doesn’t wanna sit down, he. For sure, like, I mean, you know, if you’re a parent, like two years old is very hard, but he’s not potty trained yet, so we’re not taking potty breaks with him. And then he also takes a nap and in the middle of the day, so we get that little reset, he gets a reset and he’s free since he’s under three and he’s not even quite two yet.
[00:17:45] Dana Stanley: So even under two, like the flight down, we can have him as a lap infant, also free on the flight. So he’s harder. In some ways, but it’s kind of nice that we don’t have to pay for him.
[00:17:58] Dana Stanley: All that being said, and I know that Disney people understand this, that there is pros and cons, if you wanna call it magic at every age. There have been trips where maybe my one 4-year-old, it was like a magical, easy trip, but then my other. But then their sibling, when they were four was really hard. You just don’t know.
[00:18:19] Dana Stanley: Everyone has different personalities. Every kid is struggling with different development things at different ages. So when you’re waiting for this perfect thing, or you think they’re gonna remember things, there’s always, for every plus, just know that there’s gonna be a minus. I guarantee that there’s going to be something on the trip that they lock onto and like that’s their version of magic.
[00:18:44] Dana Stanley: And it doesn’t matter if they’re like six weeks. Okay? Six weeks is pretty young. I don’t know if they’re seeing magic, but from little to nine years old, whether it be a character or seeing a train or seeing fireworks for the first time, like you can see it when it clicks for them.
[00:19:01] Dana Stanley: Like you can see it when it clicks for them. And even more than that, I think a lot of people just don’t know what they don’t know. And this next one is a perfect example.
[00:19:12] Dana Stanley: One of the biggest ones for me is booking your tickets and dining reservations First. What can happen when you skip what I call a sketch? Is now you’re kind of stuck with these concrete things like we’re visiting the parks from this date to this date and you get tickets for those days, which could be more or less than what you need.
[00:19:35] Dana Stanley: Then you have like set dining reservations that you don’t wanna cancel ’cause they were hard to get. What ends up happening is you’re like pigeonholing yourself and your plans to now fit around these things, but it should be the other way around. Most people think Disney planning is like. Any other trip, like you grab a hotel, you grab some tickets and you show up.
[00:19:56] Dana Stanley: But really without at least a loose sketch, you will, you could end up wasting a ton of time in lines missing, like big experiences that you’re hoping you could have and then spend more money fixing like last minute problems. I’ve seen this many, many times. There is one word that has changed the way I market my business completely over the years, and that word is stress free.
[00:20:25] Dana Stanley: Stress free used to be in my copy and all over my website, all over my Instagram in the beginning, and I found just as my business grew, the more I was online, the more I started talking with people and learning even more about Disney planning. And going to Disney World more,
[00:20:43] Dana Stanley: you know, it was like a disservice to say, you know, join laid back magic for a stress-free Disney trip. Or I’ve seen a rent this stroller for a stress-free trip. Or hire this travel agent for a stress-free vacation.
[00:21:00] Dana Stanley: And that’s the mistake of thinking. If I just do this one thing, if I just kind of hand this off, that your vacation itself will be free of stress.
[00:21:11] Dana Stanley: Can it lessen the stress? For sure. Can it make the planning itself less stressful? A hundred percent. But the vacation itself, especially with kids traveling in general is going to be a lot on your stress levels. It just is. It’s a lot to think about at once. There’s a lot going on all at once. It’s a long day.
[00:21:39] Dana Stanley: Even if you’re taking breaks, it’s just an unusual day that you aren’t used to, that your kids aren’t used to.
[00:21:45] Dana Stanley: You’re gonna have your kids and family. Maybe you’re in like a little studio together 24 7, which honestly is like pretty close to my normal, but I know it’s not for everyone. And that can be like a pretty stressful experience if you’re not used to it.
[00:21:59] Dana Stanley: And if you’re anything like me of just like being in a woman’s body when she had a kid.
[00:22:05] Dana Stanley: Two, three, even four years ago. Like there are chemicals and hormones that, like there are chemicals and hormones that you, and I don’t even understand what is going on, like the turmoil inside of us. And I’m pretty sure no service in the world can take that away.
[00:22:25] Dana Stanley: So can these things lessen the stress, especially like all compounded together? Yes. But don’t set the expectation that the trip is going to be stress free. That’s just a crazy thing for anyone to try and promise or g.
[00:22:42] Dana Stanley: But don’t set yourself up with the expectation that because I did X, Y, Z or used X, Y, Z, this trip is going to be stress free. I feel like that’s just a crazy thing for anyone to try and guarantee
[00:22:57] Dana Stanley: if any of these things. Made your stomach twist a little. That is not a sign that you think or you’re doing anything wrong. It just means that you care about your trip, which is great. I’ve made some of these mistakes too, and that’s exactly why I created Laid Back Magic in the first place, so that there was like, so that I could have a clear roadmap that I could repeat for every single trip with the actual steps to take, so I knew what to focus on and when all in one place.
[00:23:29] Dana Stanley: I’ll link it for you below, or just head to laidbackmagic.com and use the word podcast to get a special price as a thank you for listening to the show.
I've planned our family vacations to Walt Disney World, ranging in ages, sizes, and circumstances; without kids, with one kid, and now with two! From these trips, I've learned what not to do and want to share them with you.
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